Room For One More?
by Kashmir Winchester
Summary: Gina Pompei is a senior in Stanford College, with her roommates/bestfriends Sam Winchester and his girlfriend Jessica Moore. She's a carefree golden girl who wants to finish University and go back to Italy, where she was born and raised. So what happens when Sam's rebellious brother Dean moves and she suddenly feels like what she knows about life isn't good enough to make her happy
1. Prologue: Judging

Story title → _Room For One Mor__e?_

Pairings → Dean/OC, Sam/Jess

Type → AU

Rating → T for language

Summary → Gina Pompei is a senior in Stanford College, with her roommates/bestfriends Sam Winchester and his girlfriend Jessica Moore. She's a carefree golden girl who wants to finish University and go back to Italy, where she was born and raised. So what happens when Sam's rebellious brother Dean moves and she suddenly feels like what she knows about life isn't good enough to make her happy? AU Sam/Jess, Dean/OC (Very bad summary!)

**Disclaimer**** → I own nothing which is in any way featured ****on or related to 'Supernatural'. I only own Gina and the rest of the Pompeis.**

**Yet another new fanfiction idea that decided to pop in my head while I was at work counting new stock and replenishment. And in case you were wondering, my other in-progress stories—'Baby's Got Blue Eyes' and 'Save Yourself—are on a semi-hiatus because of writers' block and... other stuff.**

**This chapter is a sort of introduction to get to know Sam, Jessica and Gina (my OC), which is why it's so short.**

* * *

Prologue: Judging.

_To: Samuel Winchester_

_From: Dean Winchester_

_Subject: Hey_

_Hey, Sammy... Long time no talk. I know it's been over two years, but I need your help. Dad cut me off and I need a place to stay until I find a decent job, then I can move out. I'll be catching the 4 pm bus to Palo Alto, so I'll be at the station at around six if there's no traffic. Can you come pick me up? I have no fucking idea how to get to your place._

_Call me._

_Dean._

* * *

_To: Dean Winchester_

_From: Samuel Winchester_

_Subject: Re: Hey_

_I attached the map to get to my place. I don't have a car and Jess' car (two-seater) at the mechanic's. I hope you don't mind sleeping on the couch til we can afford to buy you a decent bed._

_Can't call. Five hours straight of lectures. CU at my place for dinner._

_Sam._

_PS. Try not to get arrested on your way over._

* * *

Sitting round the kitchen table, Sam Winchester, his girlfriend Jessica Moore and their roommate Gina Pompei stared down their cards, brows furrowed. Jessica was the first to make a move, taking a card—ace of diamonds—from the deck. Frowning down at it, she placed it in the middle, and looked over at Gina. She took a card from the deck, placing it in the middle of her fan of cards and placed a queen of spades on Jessica's card. Sam grinned, taking the card in his fan and after sorting them, he spread them on the table.

"Gin!" he exclaimed. The girls groaned and threw the cards on the table.

"I was so close!" Gina protested. "All I needed was an ace of clubs!"

"Face it, Gi." Jessica told her. "Sammy will always win at Gin. We should ban this game from being played of Sam's also playing." She gave him a playful glare before they leaned and kissed softly on the lips. "So who's gonna cook dinner today?"

Immediately, Sam and Jessica put a finger over their nose and yelled, "Not it!"

Gina was barely halfway. "Ah, crackers!" she moaned. It's not that she hated cooking, it's that she was always the last to yell 'not it'. Her reflexes were never good at that. She stood up and filled a pot with water, put it on the burner and lit the cooker. She could only cook one thing: spaghetti Bolognese. "So, spag bol for the second night in a row?"

"It's better than us cooking anyway. All we do is heat pizzas or order takeout." Sam winked. He looked at the time on the oven. It was nearly seven and Dean wasn't anywhere to be seen and wasn't even picking up the phone.

"But I want to heat a pizza or order takeout." Gina replied. "How do you feel about a double cheese pizza with extra spicy sauce and extra toppings sound?"

"Order a meat lovers' for Dean." Sam replied as Gina picked up her phone.

"Speaking of Dean, what time did you say he had to be here?" Jessica asked him, putting the deck of cards into their packet. She opened a kitchen drawer and placed them there, closing it with her hip.

"Well, assuming he caught the 4 pm bus to here he should've been here about an hour ago." he replied, looking at his wrist watch. "He must've stopped at a bar on his way."

Gina rolled her eyes. From what Sam had told her and Jessica over the couple of years they'd know each other, she immediately pegged Dean as a douchebag who slept with so many woman there should be a world record just for that... and he'd win it. He was also an alcoholic who lived on his dad's fame—he was a district mayor—and fortune. So she didn't get it when Sam told them his dad cut him off and agreed to let Dean stay with them until he found a job and his own place.

"He's using you, Sammy. He's using you to get free food and shelter." she'd told him. Sam had decided to give him one last chance, because he knew who his brother was now wasn't who he really is.

Noticing Gina rolling her eyes in the background, Jessica told her, "Just give him a shot. If he's the jerk you thought he was then we'll make sure he doesn't stay long here."

Jessica, always the peacemaker. If she had to choose between black and white to save her life, she'd say monochrome. This was one of the main reasons everyone loved her. All through her childhood and high-school, she was the popular, cheery girl everyone loved. She met Gina during a holiday in Palm Springs just after freshman year in high-school, and stayed in touch until they moved in together before college, which was when she met Sam at the Stanford orientation visit.

The three became inseparable ever since. Sam was aspiring to become a lawyer, having applied to all big-time law schools as far as New York. Jessica has her eye on an arts' school just outside New York. Gina, on the other hand, wanted to study psychology and then move back to Como, Italy—her birth place—once she graduated University. The idea confused her parents a little, since they moved to the US for a better life, so why would she want to move back to Italy?

Gina looked over at Sam and Jess, who were clearing the living room from their books and folders and sighed. She didn't want to judge Dean—she hated judging people she didn't know and never met in her life—but Sam made it very clear he was a jerk. A broke jerk who, judging from his past behaviour, deserved being cut off from the family fortunes.

She really didn't want him under the same roof as her.

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**So what do you think so far? I know Dean seems like a jerk in the next several chapters, but keep in mind he's that typical sibling who doesn't follow his parents' dreams. But don't fret, readers: he'll have a change of heart later on in the story (if people read and review, that is!).**

**5 reviews = new chapter! So if you like this story review, review, REVIEW!**

**Until next time!**


	2. Chapter 1: Observing

Chapter 1: Observnig

Gina's POV

This was infuriating. Why was _I _to be nice for that douche? Yes he's my bestfriend's older brother, and I don't even know him, but he brought this upon himself. He's not only homeless, but also unemployed and very broke. When he walked into the house, I could smell the reek of alcohol from across the hall while I was serving the pizzas.

However, when Sam walked into the kitchen with him, I froze to the ground. He was... gorgeous! Why are the douchey ones always so damn good-looking?! Of course he was gorgeous: his dad in the younger days was—why am I fantasising about my bestfriend's dad?! Totally inappropriate!

"Gina, this is my brother, Dean." The stare Dean gave me made me want to slap him across the face so badly! He was freaking analysing me like I'm a prize of some sort! Stupid, attractive, hot bastard. Wait a second... did I just consider Douche—the name's too good to belong to him—as hot and attractive? IN THE SAME SENTENCE AS BEING STUPID AND A BASTARD? Somebody call 911. I just committed the ultimate crime. "Dean, this is Gina. She's Jessica's bestfriend and, well, mine too."

"Damn, if you told me you had two hot girls living with you I would've definitely considered college." Dean smirked, hands on his hips, nodding approvingly at me. I raised an eyebrow. Was this dude for real? Like, legit real?

I looked over at Sam, smiling politely. "Sam, can I talk to you for a second?" This time smiling fakely, I glanced at Dean. "Alone?"

Giving Dean an apologetic look, Sam told his brother, "You mind?"

"Not at all, Sammy." he shrugged.

"Don't call me that. I'm not twelve anymore, Dean." Sam chuckled, and Dean simply left the room without a word. Sam looked back at me. "What's wrong, Gi?"

I took a deep breath. It's never easy to tell your bestfriend what you think about his brother, especially if it was bad. "Sam, you're my bestfriend. And you're also like a brother to me, so I'm just gonna tell you..." I paused. "I don't like your brother." Sam's smile faltered a little, but he looked neither angry nor upset. Just surprised I was so brutally honest, because I'm never this blunt. "I promise I'll try be nice to him but it's gonna be hard. Because he's a douche."

After a short moment of silence, Sam smiled and I sighed with relief. So he wasn't pissed at me! "Well, you're right: he _is_ a bit of a douche. But he's also the nicest, funniest person ever."

"With that badass façade of his I highly doubt he's nice." I rolled my eyes. "And he also calls you Sammy. You definitely don't look like a Sammy." I winked. Neither me nor Jess call him that, not even to joke around or anything.

"Just... be nice during dinner, please? For you bestfriend's boyfriend?" And then the puppy eyes. God, if there was one thing I had to hate about Sam was his ability to melt the anger and frustration away with one smouldering look.

"Fine."

What the hell was I supposed to say?

* * *

I observed him all through dinner. He didn't seem to realise it, obviously, deep in a conversation with Sam and Jessica. So far into dinner—fifteen minutes—he openly mentioned five girls he'd slept with in the past week. _FIVE_! Like it was no big deal! I didn't even sleep with five men in my whole life, and this guy just waltzes in and be like 'Oh, I'm Dean Winchester, I've slept with five and possibly more women in the span of a week. Yadi yadi ya...'

What a man whore.

"What?" I blinked, realising I was gazing at him. He smirked crookedly. "You were gazing at me."

"I wasn't gazing. I was... mentally trying to disintegrate your one brain cell." I smiled brightly. Sam glared at me. "What? You didn't say anything about lying."

"Gina." Jessica told me in a warning tone. I glared at Dean, who looked slightly hurt. Well tough, Dean Winchester. You hurt girls feelings and now it's your turn to take the cake. I stood up, plate in head. "Gi, where are you going?" she asked me.

"In my room. I need to study for next week's test and I'm far behind." I murmured, not making eye contact with anyone. "Enjoy or whatever..." And with that I stormed off the kitchen and inside my room, closing the door behind me. I fucking can't stand Dean much longer. Barely a night in and he's already doing his job, that is pissing me off. "Who does he think he _is_?! Casanova wannabe."

I had this habit of talking and mumbling alone, even in front of people. I had to go to therapy back in Italy in my pre-teens, but after a tough couple of years—low self-esteem, bullying and all that—i was back to murmuring to myself. It was like my head's inbox was already full of thoughts and the remaining had to be spoken.

"Okay, John Donahoe. Let's finish this darn book before midnight." I smiled, picking up the book from the floor as I placed the plate on the bedside table. This wasn't the first time I ate in my room. Most of the time I did it when I had a big test and wanted to continue studying... you know, not to break the study plan. As I was about to begin reading the next chapter, I heard Sam and Jess laughing hysterically from the kitchen, probably at something Douche said.

"Shut up!" I yelled, but I was obviously ignored, as the laughter grew.

"You should tell Gi this story!" I heard Jessica say.

"_Beh, io non la voglio sentire_!" I angrily yelled back in Italian. It was hard not to be pissed at the moment. He wasn't only distracting my study time, but also stealing my friends. Well, basically he's stealing Jess because Sam's his brother. But still! He's the _stranger_ in the building! And a douche, but that's already established.

"What did she say?" Jessica asked Sam.

"Probably something to do with me." Dean said. He did sound slightly hurt, but whatever... he's a douche. Always and forever will be.

* * *

I downed a slice of pizza with frustration as random thoughts about Dean—Douche, sorry—ran through my head. I don't know why I was even _acknowledging_ him in the first, but sure enough, as I was studying behaviour, the first person that popped in my head was him, as I came up with a theory as to why Douche was such a douche.

It was only a few weeks before the ten-year anniversary since Mrs Winchester's sudden death. Sam was only eleven, and I assume Dean was roughly in his early teens... probably fourteen years old. Her death might have put on a very unneeded weight on his shoulders, as he was still young, about to start exploring the ups and downs of teenage life. The book I was currently reading, _Learning and Complex Behavio__r_, and general knowledge, point out that most bad behaviour come out of a traumatic event.

Sam was always saying how his brother wasn't like this when he was younger, but when their mom died, Dean lost the plot and turned to stealing, smoking, drinking and sleeping around.

I sighed. "I'm such a bitch." I whispered, biting my lower lip. Maybe if I got to know the poor kid... he may still remain the douche who slept with more women than any guy I know, but deep down he's better than that.

I just need to be nicer to him... for Sam, for Jess... for him.

* * *

_**[Io non la voglio sentire = I don't want to hear it.]**_

**Hope you liked this chapter! Please bear with me: I just finished my exam, which meant hours of intense tuition and studying, and lots of work-related stress and in the midst of that, I tried to make this chapter long enough to satisfy y'all until I get a further FIVE review for this chapter. So if you like where this story is going, review and you'll get a new chapter sooner than you can say ALLONS-Y!**

**I know Gina seems a bit bitchy but don't you worry kids: there will be some change in character very soon! I also changed Gina's physical appearance (re: story cover image) so she'd look more Italian.**

**Remember to review my other stories as well: It's a Terrible Life, Baby's Got Blue Eyes and Save Yourself. Chapters are all being written but there is no definite time when these will be published, but reviews definitely help :) !**


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